N-chloro and N-bromosaccharins:: Valuable reagents for halogenation of electron rich aromatics and cohalogenation of alkenes

被引：37

作者：

de Souza, SPL ^{[1
]}

da Silva, JFM ^{[1
]}

de Mattos, MCS ^{[1
]}

机构：

[1] Univ Fed Rio de Janeiro, Inst Quim, BR-21945970 Rio De Janeiro, Brazil

来源：

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY | 2003年 / 14卷 / 05期

关键词：

cohalogenation; aromatic halogenation; N-halosaccharin;

D O I：

10.1590/S0103-50532003000500021

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-Chloro- and N-bromosaccharins react with electron rich aromatic compounds (anisole, acetanilide, N,N-dimethylaniline) producing halogenated compounds. The reaction with N-bromosaccharin gives para-substituted compounds only, whereas N-chlorosaccharin produces orto and para mixtures (para isomer predominantly, ca. 4-5:1). The reactions of the N-halosaccharins with alkenes (cyclohexene, styrene, alpha-methylstyrene, and 1-hexene) give the corresponding halohydrins.

引用

页码：832 / 835

页数：4

共 19 条

[1] N-CHLORO NYLONS AS POLYMER REAGENTS
SCHUTTEN.H
KLUMP, G
KACZMAR, U
TURNER, SR
SCHULZ, RC
JOURNAL OF MACROMOLECULAR SCIENCE-CHEMISTRY, 1973, A 7 (05): : 1085 - 1095
[2] Photoredox-Initiated 1,2-Difunctionalization of Alkenes with N-Chloro S-Fluoroalkyl Sulfoximines
Prieto, Alexis
Diter, Patrick
Toffano, Martial
Hannedouche, Jerome
Magnier, Emmanuel
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (03) : 436 - 440
[3] N,N',N'',N'''-FUNCTIONALIZED ELECTRON-RICH ALKENES AND THEIR ROLE IN TRANSITION-METAL CHEMISTRY
CHAMIZO, JA
LAPPERT, MF
ADVANCES IN METAL CARBENE CHEMISTRY, 1989, 269 : 47 - 58
[4] Chloro and Azido Diruthenium complexes Bearing Electron-Rich N,N′,N"-Triphenylguanidinate Ligands
Pap, Jozsef S.
Snyder, Jamie L.
Piccoli, Paula M. B.
Berry, John F.
INORGANIC CHEMISTRY, 2009, 48 (20) : 9846 - 9852
[5] PSEUDO-HALOGENS .21. N-CHLORO AMIDES WITH ELECTRON-WITHDRAWING GROUPS ON NITROGEN
COTTRELL, SC
ABRAMS, C
SWERN, D
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1976, 8 (01) : 25 - 32
[6] THE SYNTHESIS OF QUINOLINES FROM N-ALKYLFORMANILIDES AND ELECTRON-RICH ALKENES
METHCOHN, O
TETRAHEDRON LETTERS, 1985, 26 (15) : 1901 - 1904
[7] N,N-dimethylacrylamide-triflic anhydride complex as a novel bifunctional electrophile in reaction with electron-rich aromatics
Nenajdenko, VG
Baraznenok, IL
Balenkova, ES
TETRAHEDRON, 1996, 52 (40) : 12993 - 13006
[8] Mild and regioselective iodination of electron-rich aromatics with N-iodosuccinimide and catalytic trifluoroacetic acid
Castanet, AS
Colobert, F
Broutin, PE
TETRAHEDRON LETTERS, 2002, 43 (29) : 5047 - 5048
[9] Electron-Rich, Lewis Acidic Diborane Meets N-Heterocyclic Aromatics: Formation and Electron Transfer in Cyclophane Boranes
Widera, Anna
Filbeck, Erik
Wadepohl, Hubert
Kaifer, Elisabeth
Himmel, Hans-Joerg
CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (15) : 3435 - 3440
[10] One-pot Tandem Reactions for Direct Conversion of Thiols and Disulfides to Sulfonic Esters, Alcohols to Bis(indolyl)methanes and Synthesis of Pyrroles Catalyzed by N-Chloro Reagents
Veisi, Hojat
Ataee, Meral
Fatolahi, Leila
Lotfi, Shahram
LETTERS IN ORGANIC CHEMISTRY, 2013, 10 (02) : 111 - 117

← 1 2 →